


The Asshole Jock

by thegreatficmaster



Series: Supernatural Collection [118]
Category: Supernatural
Genre: Angst, Cocky Dean Winchester, F/M, Flirting, Fluff, Gen, Jealousy, Love Confessions, M/M, Reader-Insert, Teasing, Teen Dean Winchester
Language: English
Status: Completed
Published: 2019-08-16
Updated: 2019-08-16
Packaged: 2020-09-02 04:35:44
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,116
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20270101
Author URL: https://archiveofourown.org/users/thegreatficmaster/pseuds/thegreatficmaster
Summary: Of course your teacher would make you work with Dean Winchester. Why wouldn’t she put you with the asshole jock?





	The Asshole Jock

“Hey, y/n”.

You looked past the door, Dean Winchester leaning against the lockers, a smirk on his face.

“Yea?”

“Wanna come back to my place? You teach me about algebra. You plus me equals S-E-X?”

You rolled your eyes, slamming the locker shut.

“Screw you, Winchester!” you yelled over your shoulder, shaking your head as he let out a raucous laugh.

“Immature asshole”.

“Y/n. Sarah. I’m sorry to do this, but Dean will have to work with the two of you”.

You clenched your jaw, already so damn pissed this asshole had transferred to your school.

You’d been paired with Sarah for projects for years. You worked amazingly together.

Then that damned Winchester had to join your school.

He gave your class an odd number. He was a fucking asshole. And now you’d have to see his face every day for the next two weeks.

“Fucking great!” you mumbled as the teacher instructed Dean to go over to you and Sarah.

As soon as he made eye contact with you, a cocky grin appeared on his face as he sent you a wink.

God, you hated everything about him.

His stupid smile. 

His stupid shiny eyes. 

His dumb sexy face.

“Y/n. Guess we’re just meant to be”.

“Fuck you, asshole”.

Sarah glared at you, kicking you beneath the table.

But you didn’t care.

Dean Winchester was an asshole and you’d never like him.

“Well, move up. Unless you wanna sit on my lap, sweetheart”.

You were so close to punching him in his pretty face, but you weren’t about to ruin your school reputation.

100% attendance. You’d never had a day off.

You were top of your class in everything, and there was no way you’d let Dean Winchester mess anything up for you.

You’d just have to deal with his presence without murdering him.

You tapped your foot impatiently on the floor, looking around and hoping you’d see him turn the corner soon.

“Where the fuck is he?”

You checked your phone again, the text he’d sent last night saying he’d meet you at five.

He was half an hour late.

You waited at the bench for almost fifteen more minutes, before you got tired of it and stormed off, quickly calling Sarah.

“Hey, Sarah. Dean’s not joining us I guess. I’ll be at yours in a few minutes”.

You hung up, getting into your car and slamming the door, knowing he’d have done something like this.

“Fucking asshole”.

“I knew this’d happen”, you grumbled, pulling your books out of your backpack and switching the computer on.

“I mean, it’s not so bad”, Sarah reasoned, placing the brownies and bowls of ice-cream on the desk.

“Ooh, gimme!”

She chuckled, handing you the ice-cream as you shoved a spoonful in your mouth right away.

“I just-fuck!”

You screwed your eyes shut, the brain freeze making you wish you weren’t so damn greedy.

“Moron”, Sarah laughed, sitting on the floor beside you as she began stirring her ice-cream.

“Bitch, shut up!”

You waited for the pain to pass before you looked at her, a smirk on her face.

“Anyways, I’m just saying, I don’t know why I thought he’d be here. It’s Dean fucking Winchester. I knew a girl who was at the school he went to before he transferred, and she said he practically flunked all his classes. He barely concentrated. He was an arrogant asshole. And a straight up slut”.

She snorted, the ice-cream dripping out from her nose.

“Y/N!” she yelled, making you roll around, laughing your ass off.

“You’re such an ass”.

You continued laughing, watching her clean her nose up, before you calmed down.

“He’s really not that bad”.

You shot her a look, not understanding how she could like him.

“He was put with us to work on our project. And he didn’t even show up. I waited for almost an hour, Sarah. No text. No call. And you really think he’s nice?”

“I’m just saying, maybe he had something to do?”

“Whatever. All I know is, if he doesn’t show up next time, I’m not letting him take credit for our work”.

“Aren’t you looking gorgeous today?”

Sarah smiled, a blush rising on her face.

“Really? That’s really gonna work on you?”

She elbowed you, still smiling at Dean.

“Thank you, Dean. You look extra nice today”.

You looked him up and down, not understanding how he looked any different to yesterday.

“Thanks, Sarah. Y/n? Wanna tell me how hot you think I am?”

You scowled at him, before putting your hand up.

“Yes, y/n?”

“Miss, he’s bothering me. Can you tell him to go away?”

The teacher stared at Dean expectantly, waiting until he walked away from you, before turning back to the board.

“Why did you do that?”

“Because, he didn’t help with the work last night. He didn’t tell us why he wasn’t there. And now he thinks he can just come over and try to flirt so he take credit? I don’t think so”.

The rest of the lesson passed, you avoiding the eyes that were burning a hole into the side of your face.

You wouldn’t feel bad. 

If he really thought he could just use you to pass this project, he had another thing coming.

“Hey, y/n! Wait up!”

You ignored his calls, walking faster down the corridor as you tried to avoid him.

But of course, he caught up to you, grabbing your arm lightly and turning you.

“Didn’t you hear me?”

“Yes, Dean. I heard you. But I have better things to do than listen to you comment on how delicious your dick is or whatever perverted shit you have to say this time”.

His face fell slightly at your tone, letting go of your arm.

“I-I wasn’t gonna say that. I just wanted to know what time I should come around tonight”.

“You know what, Dean? I couldn’t care less whether or not you show up. If you wanna work, come to Sarah’s at six. If you don’t want to, I don’t really give a shit. It’s not like you showed up last night. I’m not really expecting much this time”.

His eyes widened, totally forgetting that he was meant to go over last night.

“I-I can explain”, he stuttered, walking alongside you.

“Go on”.

“I-I had soccer practice”.

You shook your head, knowing damn well he was lying as you began walking away, Dean following behind you.

“Sure, Dean. If that’s the best excuse you have, fine. We both know there was no soccer practice last night. And to be honest, I don’t really care what you were doing. All I know is, I already knew you’d be a no-show. You’re Dean Winchester. It’s not like I’d have any faith in you”.

He stopped in his tracks at your words, watching you walk off as he sighed.

Of course you wouldn’t have any faith in him.

No one did.

Why would you?

“I guess I win!”

You held your hand out, Sarah reluctantly handing you twenty dollars.

“You really need to stop with the blind faith in people, Sarah. It’s nice that you wanna believe in him. But there are times you need to realize some people value sex and parties, over actually doing something worthwhile with their lives”.

You proudly folded the note up and put it in your bag, happy that you managed to make some easy money.

“So, do you wanna do start on the intro and the conclusion? And I’ll start the research so we can get right to it later?”

Sarah nodded, beginning to work as you looked through book after book, folding the pages where they had the relevant information.

Almost half an hour passed, when you heard the doorbell ringing, Sarah’s mom going to get the door.

You paid no attention to it, until you heard the familiar voice getting closer and closer.

“They’re just in there, sweetie”.

“Thank you, ma’am”.

The door opened and Dean smiled at you nervously.

“Dean?”

“Hey, Sarah. Thought I’d stop by. Help out a bit”.

The silence in the room was suffocating, Dean obviously expecting you to say something.

“I-uh-I got some pizza. Pepperoni and plain. I don’t know what you like, so I got both”.

“Oh, you didn’t have to do that”, Sarah insisted, getting up and taking the pizzas from him and placing them on her desk.

“It’s the least I could do, for forgetting to come over last night”.

Dean looked over at you, lying on the floor on your stomach as you scanned the book, highlighting what you needed.

“You want some, y/n?”

“No thanks”.

“I’m gonna get some plates. I’ll be right back”.

Sarah left you and Dean alone in the bedroom, the awkward silence growing.

“So, what do you want me to do?”

You looked up, a small smile on Dean’s face, before you looked back down at the book.

“You just sit there. I doubt you’ll be much help”.

Dean sighed, sitting on the floor beside you.

“Come on, y/n. I’m sorry I missed yesterday. But I promise, I’ll help you from now on. I can-I can do the research if you want? Or-or, I can help type it all up?”

You didn’t look back at him, turning the page as you kept scanning.

“Just-just give me a chance, y/n. I know you think I’m some dumb jock who fucks about and doesn’t do shit. But I can’t fail this year. And I really need your help if I’m not gonna flunk out?”

You looked at him, his eyes pleading with you.

“Why am I such a nice fucking person?”

He grinned at your question, knowing you were willing to help him out.

“Thank you so much, y/n. I promise, you won’t regret it”.

You just nodded, turning back to the book as he busied himself in his bag, a small smile on your face that you made sure Dean didn’t see.

Dean Winchester had officially exceeded expectations.

For the past two weeks, he’d managed to actually show up to all the study nights.

He’d done his fair share of work. Found and written up the research.

All while never complaining and supplying you with a constant stream of food.

Today was the last day you had to work on the project.

You were almost done.

All you had to do was clean up the presentation, finish the poster and hope that the model you’d made would dry by morning.

You’d never admit it, but you loved working with Dean.

Beneath all the asshole shit he did, he was a sweetheart. And you’d be lying if you said you didn’t feel a little something for him after spending so much time together.

You were running late to get to the house, having to stay behind for a class president meeting.

You were anxious to get back, but you knew there wasn’t too much to do and Dean and Sarah would hopefully be able to get on without you.

As soon as the meeting was done, you rushed out, the time already having passed six.

You drove as fast as you could, quickly parking and jumping out.

Sarah’s mom ran into you at the door, letting you in and telling you to go straight up.

You thanked her, before making your way to Sarah’s room.

As you walked to the door, you noted the silence coming from in there.

You smiled, thinking they were concentrating on the work.

Of course, as soon as you opened the door, that thought was proved wrong.

There was Dean, sat on the chair with Sarah in his lap, lips locked together, his hands gripping her hips tight, hers wrapped around his neck.

Of course he’d be kissing Sarah.

Why would he like you?

Sarah was the blondie with blue eyes. Pretty and exactly what the guys wanted.

Of course he didn’t want you.

But you wouldn’t let either of them know just how hurt you were.

Slamming the door shut, Sarah jumped off his lap, both of them looking at you wide eyed.

“Don’t let me stop you. As long as you finish off the work, you can fuck like bunnies”, you said, your voice as even and calm as you could get it.

There was an awkward tension in the air as you sat at the computer, feeling both pairs of eyes on you.

But you wouldn’t react to it.

You knew you were right all along. 

Of course he wasn’t the nice, sweet guy he made out he was.

Deep down, Dean Winchester was a womanizing asshole who just used you to get a good grade. 

You were just glad nothing happened between the two of you, even if you slightly wished it had.

“Hey, y/n”.

You looked up, Sarah standing in front of you, a strained smile on her face.

“Hey”.

You stared at her, wondering what she was doing.

“What is it?” you asked after a minute of nothing.

“I-are we ok?”

You frowned at her, tilting your head slightly.

“Why wouldn’t we be?”

You knew exactly what she was talking about. But you were trying to forget about Dean Winchester, and you weren’t about to let what happened last Friday affect you.

“I just-about what happened on Friday. Dean-he didn’t want it. I-he was kinda pushing me off after a few seconds and then you walked in”.

“And you’re telling me this, why?” you asked, not believing a word she said.

She sat opposite you, looking around for the librarian, before she began talking again.

“I just-I’m sorry we did that. And I’m sorry you saw it. It didn’t mean anything. It was just the heat of the moment. He’s cute, but I don’t like him. And I’m pretty sure he doesn’t like me back because there’s someone else on his mind”.

You nodded, a disinterested look on your face.

“Ok. Well, thanks for apologizing. But-I’m fine. I saw you kissing. It’s not the end of the world, Sarah”.

She shook her head, her hand gripping yours.

“Y/n, I know you like him. And I-I know he likes you too”.

You scoffed, about to deny all of that, but she spoke before you could.

“But I was jealous, ok? I-I just wanted him to want me. All those nights we were at mine, his eyes were always on you. He barely heard a single thing I said, because he was so focussed on getting you to like him. And maybe it’s an awful thing, me trying to get with him when I know you like him, but I just wanted him to see me”, she rambled, her hands flailing everywhere as she spoke.

“But he doesn’t. The kiss didn’t feel right for either of us. And when you walked in, he was pushing me off his lap. And after you left, he made it clear that there was nothing between us. That he had someone else on his mind”, she trailed off, wishing you’d finally accept your feelings.

Btu of course, you were too stubborn for that.

“Like I said, Sarah. I really don’t care. And if he has someone else on his mind, let him get with her. Pretty sure she’ll be out of his mind and replaced by the next blonde who’ll spread her legs for him in a weeks’ time anyways”.

She sighed, shaking her head at your stubbornness.

“I know you think he’s just some dumb jock who sleeps around and does nothing but watch football all day, but he’s a nice guy. You know it. And so do I. And he’s told me how much he likes you. So, stop being a stuck up moron and don’t deny your feelings. Because we both know you like him just as much as he likes you”.

The next few weeks consisted of you avoiding Sarah and dodging Dean every time he saw you.

You knew Sarah was right. 

You liked Dean.

A little too much.

But you were so sure he was just a dumb jock.

You thought if you managed to go out with him, he’d take you out on a single date, fuck you, and then ignore you forever.

He was that kind of guy.

Right?

Everything in you told you he wasn’t. 

The weeks you’d spent with him, you got to know him.

He was sweet. Kinda dorky. Adorable. Just perfect.

But your head was so determined to keep him out.

You were the golden student.

You were the one who’d get a free ride to college. 

You were meant to be the one who made it out of the small town and made it big. 

It’s what you always dreamed of.

And nowhere in those fantasies was there a jock who was failing most of his classes, would most likely go to a football college, and probably not make too much of his life.

He just wasn’t right for you.

So why did everything else in you scream for him?

You knew where he’d be.

Apparently, Dean would practice well into the night, even after the coach and the rest of the team would leave.

You knew you’d probably been keeping him from practice for the past few weeks.

Hopefully you hadn’t hurt his chances of getting into a football college.

You walked out onto the field, Dean throwing the ball as far as he could, before picking up another, then another, then another.

“You’re gonna throw your arm out if you don’t rest soon”.

Dean turned swiftly at the sudden voice, a sigh of relief leaving him when he saw you.

“Dammit, y/n!”

You giggled, smirking at him.

“Did I just scare the big strong jock?” you teased, grabbing one of the balls and turning it in your hands.

“No! It’s just pitch black and when someone sneaks up on me, I tend to get defensive”.

“That’s good to know. You’ll protect me and die, while I run away. Right?”

He shook his head in amusement, raising an eyebrow.

“Can I help you, y/n? Not that I’m complaining. But why are you here?”

You shrugged, moving in front of him and throwing the ball as hard as you could.

Of course, it didn’t get too far. You weren’t big on sports.

Dean sniggered at your attempt, making you frown.

“What? It’s not like I play every day”.

He held his hands up, smiling at you.

“Hey, hey. I didn’t say a single thing. It’s just, you’re standing completely wrong. And there wasn’t enough power in your throw”.

You stood there, waiting for him to move, before you flapped your arms.

“Well? You gonna show me?”

He bit his lip, moving behind you until he was pressed up against your body.

You shut your eyes at his warmth, the smell of his sweat being so intoxicating to you in that moment.

His hands gripped your hips, moving you slightly, your legs being positioned in the perfect stance.

His breath was hot on your neck, making the hairs stand on end.

“Legs are perfect. What you wanna do next is make sure your chest is perfect”.

You held your breath as his hands went to your waist, moving your torso.

One of his hands came to your back, pushing your chest out, then the other onto your sternum, pushing down lightly.

His hands were calloused and rough, yet they glided over your skin perfectly.

You imagined his hands running all over your body, gripping you tight as he fucked you hard, right there and then on the football field.

But, while you were craving him, especially when he was so close to you, you weren’t desperate.

His hands left your body, his heat gone as he grabbed a ball and placed it in your hand.

“Now, you throw with a shitload of power. And make sure you follow through with your arm”.

“What does that mean?”

“Just-just watch me”.

He grabbed another ball, walking so he was in your view, without you having to move too much.

“You watching?”

“Yep”.

Your eyes raked up his body, appreciating his cute ass in those tight shorts and the way his thighs looked so perfect.

Your gaze got higher and higher, the muscles in his body rippling as he pulled his arm back and threw the ball.

Your eyes weren’t focussed on the way the ball hurtled through the air, instead watching Dean grunt and smile.

“How are you so fucking sexy?”

“What?”

You blushed, realizing you’d just said that out loud.

“N-nothing”.

“You sure about that?”

You looked up at him, ready to confess all of your feelings, but there were things you needed to know first.

“Sarah. What happened that day? Do you like her?”

Dean sighed, staring down at the ground, before he sat.

“Nope. She-she talked about liking me. I told her I don’t. She backed me up. I fell onto the chair. She straddled me and kissed me. I was about to shove her off me, when you walked in. I definitely don’t like her. She’s sweet. But she’s Sarah. I don’t want a Sarah”.

You could tell he was being honest, but you needed to know more.

“Ok. And you’re single? Cos, I still have no idea why you didn’t show up on that first day”.

“I didn’t show up because I was-uh-I was with my kid brother”.

“Sam?”

Dean shook his head, looking up at the sky and groaning.

“No. Adam”.

“Adam?” you questioned, never having heard of a third Winchester brother.

“Yep. My dad’s second family. My half-brother”.

Your jaw dropped.

The Winchester kids were known as trouble. 

Dean especially, Sam tagging along.

But everyone thought the parents had a perfect marriage.

“Y-your dad had an affair?”

He shook his head, swallowing thickly.

“No. My mom had an affair. Dude named Arthur. And my dad found out. Apparently they separated when we were kids. I don’t remember it, but it happened. Dad found someone else. Mom was single. Then she wanted to try again and Dad came back. I guess the woman Dad was with had a kid, but didn’t want to break our family apart”.

You sat down next to Dean, your arms touching as you picked grass.

“So, how did you find out about Adam?”

“Mom cheated again. Same dude. Dad decided it was the final straw. He left. Moved out and filed for divorce. Then he found Kate, the woman he was with. And he met Adam. She told him about what happened. How she felt it was better, for both us and Adam, to not bring that kind of drama into our lives. Dad accepted it. He was pissed. But I think he knew she just did what was best. But ever since, dad’s been getting to know Adam. He stays there a lot. They’re dating again. And even if I’m not used to the thought of having another brother outside Sam, Adam’s a nice kid. Sweet. Clever as hell. His mom did an amazing job”.

You smiled at the way he was talking about the long lost brother he’d just found out about.

You could tell Dean already loved him.

It was sweet to see a guy who constantly put on that mask of arrogance and confidence, be so open and vulnerable.

Dean stared off into space, before he spoke again.

“Anyway. That’s why I couldn’t show up. Adam wanted to see me. Oh, and I’m completely single. Truth be told…”

He indicated for you to come closer, waiting until your ear was at his lips.

“I’m kind of a virgin”.

Your jaw dropped as you moved back, staring at him.

“You? Dean Winchester? The one everyone talks about? Is a virgin?”

He shrugged, a huge smile on his face.

“What can I say? I’m just waiting for that special someone. Like I said, I don’t want a Sarah. I want a y/n”.

He stared at you, his eyes shining in the moonlight, hope and joy painted on his face.

“You’re lucky. Cos I’m pretty sure I want a Dean”.

He grabbed your hand, pulling you onto his lap, his hands snaking around your waist.

You leaned down, your lips joining in a soft kiss, tentative and sweet.

You pulled away, staring into his eyes, resting your forehead on his.

He looked at you with such softness, you couldn’t help your heart fluttering.

You don’t know how you ever doubted Dean.

He was the sweetest boy you’d ever met.

And you were glad you were his special someone.

Truth be told, Dean Winchester was officially your perfect guy.


End file.
